Potassium Hydroxide → HCID 18946290, compound

Metallic sodium (1.15 g, 50 mg-atom) was dissolved in methanol (100 ml) and 4-hydroxybenzylcyanide (6.7 g, 50 mmol) was added. The obtained solution was concentrated and acetonitrile (2×10 ml) was evaporated from the residue. The obtained salt was dissolved in anhydrous dimethylformamide (200 ml) and about 25 ml of the solvent was removed under reduced pressure. To the obtained solution N,N-dimethylthiocarbamoyl chloride (9.9 g, 80 mmol) was added and the reaction mixture was stirred at 80°-85° C. for 2 hours. Thereafter additional N,N-dimethylthiocarbamoyl chloride (2.5 g, 20 mmol) was added and stirring at 80° C. was continued for further one hour. After cooling the mixture was poured into aqueous 1% KOH (500 ml) and extracted with ether (3×200 ml). The organic extracts were washed with water until neutral, dried over MgSO4 and concentrated. The solid residue was triturated with water and after drying also with isopropyl ether to give the title compound (5.42 g), mp. 120°-124° C., yield: 52.7%.

1. concentrationThe obtained solution was concentrated
2. customacetonitrile (2×10 ml) was evaporated from the residue
3. dissolutionThe obtained salt was dissolved in anhydrous dimethylformamide (200 ml)
4. customabout 25 ml of the solvent was removed under reduced pressure
5. stirringstirring at 80° C.
6. waitwas continued for further one hour
7. temperatureAfter cooling the mixture
8. extractionextracted with ether (3×200 ml)
9. washThe organic extracts were washed with water until neutral,
10. dry with materialdried over MgSO4
11. concentrationconcentrated
12. customThe solid residue was triturated with water
13. dry with materialafter drying also with isopropyl ether

ORD record

ord-10c596923c8e4067af7532428324ebb3

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380724